CYP1A1-IN-2
CYP1A1-IN-2 (Compound 14) is a competitive inhibitor of CYP1A1 (Ki: 1.4 μM). CYP1A1-IN-2 exhibits potent antimitotic activity and arrests cell in the G2/M phase. CYP1A1-IN-2 disrupts the microtubule and the cytoskeleton in CYP1A1-expressing breast cancer cells.
For research use only. We do not sell to patients.
- CAS No.: 1422527-87-4
- Formula: C23H30N2O7S
- Molecular Weight:478.56
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biological Activity
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Chemical Information
- Protocols
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
Description
IC50 & Target
[1]|
CYP1A1 1.4 μM (Ki) |
Cellular Effect
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| HT-1080 | IC50 |
30 nM
Compound: 14
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Antiproliferative activity against human HT-1080 cells expressing CYP1A1 assessed as cell growth inhibition incubated for 48 hrs by sulforhodamine B assay
Antiproliferative activity against human HT-1080 cells expressing CYP1A1 assessed as cell growth inhibition incubated for 48 hrs by sulforhodamine B assay
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[PMID: 36780426] |
| HT-1080 | IC50 |
4440 nM
Compound: 14
|
Antiproliferative activity against human HT-1080 cells assessed as cell growth inhibition incubated for 48 hrs by sulforhodamine B assay
Antiproliferative activity against human HT-1080 cells assessed as cell growth inhibition incubated for 48 hrs by sulforhodamine B assay
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[PMID: 36780426] |
| HT-1080 | IC50 |
5900 nM
Compound: 14
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Antiproliferative activity against human HT-1080 cells transfected with empty vector assessed as cell growth inhibition incubated for 48 hrs by sulforhodamine B assay
Antiproliferative activity against human HT-1080 cells transfected with empty vector assessed as cell growth inhibition incubated for 48 hrs by sulforhodamine B assay
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[PMID: 36780426] |
| HT-29 | IC50 |
>12500 nM
Compound: 14
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Antiproliferative activity against human HT-29 cells assessed as cell growth inhibition incubated for 48 hrs by sulforhodamine B assay
Antiproliferative activity against human HT-29 cells assessed as cell growth inhibition incubated for 48 hrs by sulforhodamine B assay
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[PMID: 36780426] |
| M21 | IC50 |
>12500 nM
Compound: 14
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Antiproliferative activity against human M21 cells assessed as cell growth inhibition incubated for 48 hrs by sulforhodamine B assay
Antiproliferative activity against human M21 cells assessed as cell growth inhibition incubated for 48 hrs by sulforhodamine B assay
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[PMID: 36780426] |
| MCF7 | IC50 |
200 nM
Compound: 14
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Antiproliferative activity against human MCF7 cells expressing CYP1A1 assessed as cell growth inhibition incubated for 48 hrs by sulforhodamine B assay
Antiproliferative activity against human MCF7 cells expressing CYP1A1 assessed as cell growth inhibition incubated for 48 hrs by sulforhodamine B assay
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[PMID: 36780426] |
| MCF7 | IC50 |
38 nM
Compound: 14
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Antiproliferative activity against ER/PR/HER2-positive human MCF7 cells assessed as cell growth inhibition incubated for 72 hrs by sulforhodamine B assay
Antiproliferative activity against ER/PR/HER2-positive human MCF7 cells assessed as cell growth inhibition incubated for 72 hrs by sulforhodamine B assay
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[PMID: 36780426] |
| MDA-MB-231 | IC50 |
8600 nM
Compound: 14
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Antiproliferative activity against ER/PR/HER2-negative human MDA-MB-231 cells assessed as cell growth inhibition incubated for 72 hrs by sulforhodamine B assay
Antiproliferative activity against ER/PR/HER2-negative human MDA-MB-231 cells assessed as cell growth inhibition incubated for 72 hrs by sulforhodamine B assay
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[PMID: 36780426] |
| MDA-MB-468 | IC50 |
21 nM
Compound: 14
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Antiproliferative activity against ER/PR/HER2-negative human MDA-MB-468 cells assessed as cell growth inhibition incubated for 72 hrs by sulforhodamine B assay
Antiproliferative activity against ER/PR/HER2-negative human MDA-MB-468 cells assessed as cell growth inhibition incubated for 72 hrs by sulforhodamine B assay
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[PMID: 36780426] |
| SK-BR-3 | IC50 |
3.2 nM
Compound: 14
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Antiproliferative activity against ER/PR-negative HER2-positive human SK-BR-3 cells assessed as cell growth inhibition incubated for 72 hrs by sulforhodamine B assay
Antiproliferative activity against ER/PR-negative HER2-positive human SK-BR-3 cells assessed as cell growth inhibition incubated for 72 hrs by sulforhodamine B assay
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[PMID: 36780426] |
| T47D | IC50 |
1 μM
Compound: 14
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Antiproliferative activity against ER/PR-positive HER2-negative human T47D cells assessed as cell growth inhibition incubated for 72 hrs by sulforhodamine B assay
Antiproliferative activity against ER/PR-positive HER2-negative human T47D cells assessed as cell growth inhibition incubated for 72 hrs by sulforhodamine B assay
|
[PMID: 36780426] |
In Vitro
CYP1A1-IN-2 (Compound 14, 48 h) inhibits MCF-7 cell growth, with an IC50 of 200 nM, and is inactive on MDA-MB-231 (IC50 >8600 nM)[1].
CYP1A1-IN-2 inhibits MDA-MB-468, SK-BR cell growth with IC50s of 21 nM, 3.2 nM[1].
CYP1A1-IN-2 (50 nM, 48 h) causes accumulation of the cells in the G2/M phase by 42%[1].
CYP1A1-IN-2 shows high affinity for CYP1A1 (Ki: 1.4 μM)[1].
CYP1A1-IN-2 selectively inhibits HT-1080 cell proliferation, with IC50s of 30 nM for HT-1080 transfected withCYP1A1[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.
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Cell Line:MCF-7 cell
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Concentration:50 nM
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Incubation Time:48 h
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Result:Arrested cell in G2/M phase.
In Vivo
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Chick embryos grafted with HT-1080CYP1A1 cells[1]
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Dosage:1 μg/egg
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Administration:Applied to chick chorioallantoic membrane.
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Result:Reduced tumor weight by 49%.
Chemical Information
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CAS No. 1422527-87-4
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Molecular Weight 478.56
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Formula C23H30N2O7S
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SMILES
CCCCCN1CCN(C2=CC=C(S(=O)(OC3=CC(OC)=C(C(OC)=C3)OC)=O)C=C2)C1=O
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Protocols
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Flow cytometric DNA-content cell-cycle staining
Flow cytometric DNA-content cell-cycle staining measures the fluorescence intensity of DNA-bound fluorochromes in single cells or nuclei to estimate DNA content distributions, allowing assignment of populations to G0/G1, S, and G2/M phases by DNA histogram deconvolution. Propidium iodide (PI) intercalates into DNA, and PI fluorescence is proportional to cellular DNA content when staining is performed under conditions that make DNA accessible and minimize non-DNA signal. Cells with G2/M DNA content are expected to show approximately twice the fluorescence intensity of G0/G1 cells, while S-phase cells occupy intermediate fluorescence values. PI-based DNA-content analysis can also detect cells with fractional DNA content, often reported as sub-G1, when DNA fragmentation and extraction during staining reduce retained DNA signal in apoptotic cells. DAPI is an alternative DNA fluorochrome for univariate DNA-content analysis, while bivariate approaches combining DNA content with proliferation
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Protocol for Cell Cycle
Cell-cycle analysis by flow cytometry measures DNA content in single cells to estimate the fraction of cells in G0/G1, S, and G2/M phases. Propidium iodide intercalates into DNA, and after RNA removal with RNase, fluorescence intensity reflects cellular DNA content: 2N cells are assigned to G0/G1, cells between 2N and 4N to S phase, and 4N cells to G2/M. DNA-content analysis alone cannot reliably separate G0 from G1 or G2 from M. Ki-67 can distinguish quiescent G0 cells from cycling cells, EdU or BrdU incorporation marks active DNA synthesis in S phase, and phospho-histone H3 staining identifies mitotic cells within the 4N population.
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Breast Cancer Modeling
Breast cancer is a heterogeneous cancer, and it has been distinguished into four subtypes: luminal A, luminal B, HER2-positive and basal-like. Molecular mutations, epigenetic alterations, hormone exposure and immune microenvironment are related to the progression of breast cancer.
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Phalloidin F-actin cytoskeleton staining
Phalloidin F-actin staining detects polymerized filamentous actin in fixed and permeabilized specimens by using fluorescent phalloidin or phalloidin-derived phallotoxins that bind actin filaments and generate a fluorescence microscopy readout corresponding to F-actin organization, including stress fibers, cortical actin, filament bundles, and tissue-specific actin networks. Phalloidin stabilizes F-actin by reducing actin subunit dissociation from filament ends, and fluorescent phallotoxins were established as tools for visualizing actin-containing structures in eukaryotic cells.
Purity & Documentation
References
[1]. Chavez Alvarez AC, et al. Homologation of the Alkyl Side Chain of Antimitotic Phenyl 4-(2-Oxo-3-alkylimidazolidin-1-yl)benzenesulfonate Prodrugs Selectively Targeting CYP1A1-Expressing Breast Cancers Improves Their Stability in Rodent Liver Microsomes. J Med Chem. 2023 Feb 23;66(4):2477-2497. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
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